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The total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996

Bon, David J.-Y. D; Banwell, Martin; Cade, Ian; Willis, Anthony


The title sesquiterpenoid natural product 1 has been prepared for the first time using the enantiomerically pure cis-1,2-dihydrocatechol 3 as starting material. Key steps associated with the synthesis include a Diels-Alder cycloaddition reaction of the acetonide 5 with cyclopentenone (4) and an oxa-di-π-methane rearrangement of bicylco[2.2.2]octenone 6 derived from the initial adduct. The product of this sequence, the cyclopropannulated triquinane 7, was elaborated, over a further eight steps...[Show more]

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
Source: Tetrahedron
DOI: 10.1016/j.tet.2011.08.057


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